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Cowbell appoints Simon Hughes as Chief Commercial Officer. News provided by. Hughes to lead global commercial strategy as Cowbell accelerates its next cycle of growth PLEASANTON, Calif., Jan. 15, 2026 /PRNewswire/ - Cowbell, a leading provider of adaptive cyber and specialty insurance solutions for global small and mid-market organizations, today announced the appointment of Simon Hughes as Chief Commercial Officer. Hughes, who previously served as SVP, Global Distribution & GM, UK, will oversee Cowbell's global commercial strategy, including distribution, partnerships, international expansion, and market development. Since joining Cowbell to launch and lead the company's UK operations, Hughes has played a pivotal role in expanding Cowbell's international footprint and strengthening its distribution ecosystem. His appointment comes as Cowbell advances the next cycle of its organizational journey, focused on sustained growth, operational profitability, and continued global expansion. "Simon has been instrumental in shaping Cowbell's international presence and elevating our commercial capabilities," said Trent Cooksley, Co-founder & Chief Operating Officer, Cowbell. "As we enter this next phase of growth, his leadership across distribution, partnerships, and global market strategy will be critical to scaling responsibly while deepening our value to brokers and policyholders worldwide." "Cowbell's growth over the past several years, from launching new markets to broadening our product and services portfolio, has been extraordinary. Leading the UK launch has been a career highlight, and I'm proud of the impact our team has made across the organization," said Hughes. "As we move into this next cycle, I'm eager to help drive our global commercial strategy and continue building a platform that delivers protection with clarity, confidence, and scale." Simon's appointment comes on the heels of Cowbell's rapid momentum, including the company's evolution into a broader digital protection partner and its expansion into new international markets. The company now partners with over 35,000 producers globally and continues to grow its risk pool, product portfolio, and global reach as it advances its next cycle of strategic expansion. About Cowbell Cowbell is a pioneer in Adaptive Cyber Insurance, redefining risk transfer for the digital age. As the first platform to unify Cyber, Tech E&O, and Management Liability into a single, API-driven solution, Cowbell expedites the insurance purchasing process, with policy issuance in as little as five minutes through its proprietary, AI-powered platform and Cowbell Factors(TM)- a dynamic framework for continuous risk assessment. Serving businesses with up to $1 billion in annual revenue, Cowbell operates across all 50 U.S. states, the District of Columbia, and the United Kingdom. The company is backed by over 25 leading global (re)insurance partners, offering a comprehensive suite of coverages in commercial and specialty lines, including cyber, technology errors and omissions, and management liability. Through Cowbell Resiliency Services (CRS) - an independent cybersecurity advisory arm - policyholders gain access to Digital Forensics and Incident Response (DFIR) services as well as proactive solutions designed to reduce risk exposure and improve insurability. Founded in 2019 and headquartered in the San Francisco Bay Area, Cowbell has a global presence with teams across the U.S., Canada, Australia, India, and the U.K., driving innovation in cyber risk management worldwide. Christian Morley ICR for Cowbell [email protected]

Next cycle of growth and global expansion at Cowbell. Cowbell announced the next phase of its organizational journey, emphasizing sustained growth, operational profitability, and ongoing global expansion. Building on its recent entry into australia, the company is accelerating international growth while continuing to scale and strengthen profitability. The initiative marks Cowbell's evolution from an Adaptive Cyber Insurance pioneer to a broader digital protection partner spanning cyber, professional, and management liability lines. Building on strong performance and market expansion this year, the company's next cycle emphasizes five strategic growth drivers: international cyber, financial lines, resiliency services, mid-market expansion, and franchise subscriptions. "As we enter this new cycle, parlaying our success in new products, new services, and new markets over the past 18 months, we are poised to scale responsibly and profitably," said Jack Kudale, Founder and CEO of Cowbell. "Cowbell has built a solid foundation of technology, talent, and trust. Now, we're focusing on translating that strength into sustained growth, global expansion, and operating profitability while continuing to deliver protection that creates confidence, not complexity." To steer this next phase of strategic growth, Cowbell has appointed John Botros as Chief Financial Officer. Bringing more than a decade of financial leadership across high-growth technology and cyber-risk organizations, Botros most recently served as CFO at Resilience, where he led investor relations, strategic initiatives, financial planning, revenue operations, and board engagement for the cyber-risk solutions provider. He was named among the Top 25 CFOs in San Francisco by Finance & Investing in 2023. Most recently, he was included in Marquis Who's Who for his leadership in financial strategy and technology. Botros will oversee global finance operations at Cowbell as the company advances its next cycle of growth, profitability, and international expansion. Cowbell protects approximately 30,000 SMEs worldwide, representing a total insured revenue of $610 billion. Sixty percent of these policyholders have partnered with Cowbell for more than three years. Since its inception, Cowbell has paid over $275 million in claims and expanded its global risk pool to include 55 million small and medium-sized organizations.

Cowbell launches self-service platform for cyber risk services. The California-based insurer has introduced new dashboard capabilities allowing policyholders to access cybersecurity tools and AI compliance services on demand. (Image source: Cowbell homepage.) Cowbell (Pleasanton, California) has launched self-service capabilities for Cowbell Resiliency Services (CRS), enabling policyholders to browse, request, and activate cybersecurity risk-management services directly from their policy dashboard. The new feature is designed to streamline access to vetted digital protection tools and support more flexible, proactive cyber risk mitigation. Policyholders can now explore a range of offerings - such as managed detection and response, identity monitoring, and cybersecurity awareness training - and request services with minimal coordination. Cowbell states that all offerings are pre-vetted by its cybersecurity team and available at pre-negotiated, discounted rates. "Small and mid-market businesses have told us they want faster, more direct access to cybersecurity services, and this self-service capability addresses that need by putting enterprise-grade security tools within easy reach," comments Matthieu Chan Tsin, SVP and GM, Cowbell Resiliency Services. "Organizations can now implement protective measures on their own schedule, empowering them with the flexibility and confidence to strengthen their defenses without waiting for lengthy coordination." In addition to launching self-service access, Cowbell has expanded its CRS platform with the introduction of COMPaaS-AI, a governance and compliance service focused on responsible use of artificial intelligence. The solution is intended to help businesses align with evolving AI regulations and frameworks, including the NIST AI Risk Management Framework and ISO 42001. Cowbell states that COMPaaS-AI supports continuous compliance for organizations deploying AI technologies and is available immediately to policyholders through the CRS platform.